Dennis Eshbaugh is the President and General Manager of Holiday Valley, one of New York’s largest resorts. He came to Ellicottville in the 1970s as a ski instructor assumed his leadership position in the mid-1990s, overseeing significant growth and the transformation of the resort.
Under Eshbaugh, Holiday grew into one of the most successful ski areas in the East, adding amenities and becoming a year-round destination. He has focused on a local approach to resort management, allowing the resort to thrive without becoming part of one of the major ski pass conglomerates.
He graciously agreed to detail his rise through the company and the philosophy that has contributed to this success story.
Where did you grow up? When did you start skiing? What was your first home mountain? When did you first ski Holiday Valley?
I grew up in Erie, PA. I started skiing when I was 15, my friend Chuck Brown took me to Peek‘n Peak, which became my first home mountain. I first skied Holiday Valley in 1975, I think.
Have you skied any of New York’s lost ski areas?
I’ve skied Grosstal/Ski Wing, Eagle Ridge, Val Bella Allegany NY, Poverty Hill, Cockaigne and Little Valley Ski Slope. I visited Bluemont but did not ski there. I wish they all were still in business! Every area was unique and special in its own way. They made skiing accessible and gave everyone an opportunity to ski.
Where else do you ski? How many days a year do you get?
I try to ski over 50 days a year. I make it a point to visit a minimum of 10 different areas every year. I’ve been fortunate to ski in several Canadian Provinces, Colorado, Utah, Montana, Idaho, Nevada, Oregon and Washington in the West. At heart I’m an Eastern skier who has enjoyed too many ski areas to count in New York, Pennsylvania, West Virginia, Vermont, New Hampshire, Maine, and Massachusetts.
California is currently a favorite destination for me because my youngest daughter works at Sugar Bowl. I’ve skied Mammoth, Palisades, Alpine, Northstar, Boreal, Heavenly Valley and others. I’ve had the good fortune to enjoy cat and heli-skiing trips.
Every skier should visit Tuckerman Ravine at least once in the springtime.
If you have free time on a powder day at Holiday Valley, where do you head?
Eagle, Hoot Owl, Foxfire… chasing the snow!
What was your first job in the ski business?
As a student at Indiana University of Pennsylvania, and I did everything from lift operator to rental shop to ski school and ski patrol. My second job was ski instructor at Peek ‘n Peak.
When did you start working at Holiday Valley? What jobs have you held?
I started here in the 1975-76 season. I was a ski instructor, then director of Ski School, Project Manager, General Manager and finally President.
In your mind what are Holiday’s biggest strengths and challenges?
It starts with an incredible group of people including the hardworking staff and great leadership of the Board of Directors. We have a strong brand as a quality resort with a great variety of terrain, excellent lift system, incredible automated snowmaking (the largest HKD automated system in the East) lodging on site and (this is big) the Village of Ellicottville.
Challenges: We focus on managing the impacts of the weather in our business. It can change on the hour, by the day and every season is unique. You have to be adaptable, nimble and always ready to respond.
On a granular level, the greater challenge for Holiday Valley and the ski business in general is convincing people to take the risk, getting a share of their limited free time and then introducing them to skiing and snowboarding in a way that makes them want more. On top of all this, managing to keep a sustainable business.
How do you convert beginners into lifelong skiers?
Encourage them to bring friends to ski with and encourage them to meet other new skiers/riders. Make it affordable, convenient and desirable to take lessons.
Our eight-session ski programs for schools include lessons and kids can hang with their friends in a cool environment, without their parents! These programs are also available to adults, individuals and clubs. We also offer season-long kids’ programs (kind of like winter camp every weekend) for kids starting at age four up to teens.
The 2026 Olympic year will help get people interested in the sport.
How do you view the impact of mega-passes?
These passes are in the news often which certainly helps to keep skiing top of mind. One drawback is the expense — they discourage people who want to try the sport.
Holiday Valley is not a member of any mega-pass or reciprocals (SANY excepted). We are fiercely independent! We stay focused on what works best for Holiday Valley and our customer. I would never speak against the benefits of a multi-area pass for skiers; however, our efforts are concentrated on how to best serve the Holiday Valley skier.
How much of your revenue falls outside of winter?
Holiday Valley typically generates 20% of our revenue outside of skiing. This is consistent with most ski areas that have summer activities. Revenue generators include golf, Sky High Adventure Park/Mountain Coaster/Chairlift rides, pools, and meetings-weddings-conferences.
• Where do your skiers come from?
Business comes from the West (Ohio – 25%), North (Buffalo 30%, Canada 20%), South (PA 15%) and East (Rochester 10%)
Has recent economic tension between the US and Canada had an impact on your business?
Somewhat, mostly people who are not Holiday Valley regulars. We’ll see what the winter brings. Canadians who know Holiday Valley and Ellicottville know we love them!
What makes Holiday Valley different from other areas?
The foundation of Holiday Valley is people committed to service and having fun. We offer a top-notch quality of lifts and infrastructure. The Village of Ellicottville is a huge benefit. We have easy access from several metro areas (Buffalo, Toronto, Rochester, Pittsburgh, Cleveland). We benefit from lake effect snows and generally good weather.
Tell us about “running your business so you’re not a predator for local business.”
Our association with the genuine village of Ellicottville and the community is a huge part of our success. It’s a symbiotic relationship: Holiday Valley brings business to town, and, at the same time, the town is another reason people love Holiday Valley. We work hard to cooperate with local businesses and don’t compete with them. We stay focused on the areas where we excel.
What is Holiday Valley’s tree skiing policy?
All our terrain is open to skiing/riding and we have four designated glade runs. There is a tree skiing culture that is evident in snowy years, like last season.
What improvements are planned for the next decade?
More lifts, more buildings, more snowmaking and pickleball (Jane’s idea.)
What is the most surprising thing about Holiday Valley?
People are surprised at what we’ve done with 750 vertical feet. Due to the layout of our mountain winds around four different faces, it gives us incredible variety of terrain.
What are the top activities for non-skiing visitors?
Tubing, Mountain Coaster, shopping, dining and spas in Ellicottville, XC ski or snowshoe, visiting local Amish shops, gambling and shows at the nearby Seneca casino. Pub crawl – no just kidding (sort of). Four great independent ski/snowboard shops with excellent boot fitting. The tubing Park is great is new this year – colored lights on the hill!
Thanks for your time Dennis.
You’re welcome and thank you for the opportunity.
I like these interviews / profiles. Looking forward to more throughout the season, not just skier/rider accounts of their visits (enjoyable as those are, as well).
When my son was a ski racer in Easterns, Holiday Valley was our favorite ski resort to visit. Holiday Valley had the best lodges by far with their easy chairs and fireplaces , and definitely the best food. The race course was always in prime condition, there was a dedicated race building for the racers pand on cold days everyone enjoyed the warming hut at the top. Additionally, I could take off for a few runs with my daughter because of the easy access to all the lifts and still not miss my son‘s runs. Finally, I absolutely loved the little history display in one of the lodges, I eat that stuff up! Being in beautiful Ellicottville made all the more special. I sure miss those days. Good luck in the future, I’ll be heading there this winter.
Thanks Dennis for keeping skiing and riding fun and enjoyable for all the non mega pass holders out there! We need more of you!
Great interview – makes me want to take the trip west to check out Holiday Valley. The mention of 4 different mountain faces makes the skiing sound very attractive. Always heard very good things about HV and Ellicottville.
Very interesting article.
I find it curious that Holiday among others have logos that have the incorrect number of stems or points on the stellar type snow crystal. Ice crystals cleave at 60 degree angles—so the vast majority of stellar crystals have six (6) points. The eight (8) pointed image does not exist in nature it is an artist’s image of A “snow crystal.” The Holiday logo is cool with summer and winter represented — 4 points and 4 sun rays. It would be more accurate to show 3 point and 3 rays. (I can provide references, but to me just saying so is overkill.)
PLEASE look into buying Cockaigne and Peek N Peak! Your management could turn these hills around!
I live in Toledo, OH and learned to SKI in Michigan. My Mom’s family is from Ellicottville and nearby Salamanca. In 1972, I was 20 yrs. old, when family members encouraged me to come try Holiday Valley! Now I am 73 yrs. and I raised my kids, traveling 4.5 Hrs. every weekend, to make Holiday Valley our Home Hill! My Son who got married at the top of Morningstar, had 125 guest ride the Mardi Gras lift to their beautiful Fall ceremony! My grandkids are now Holiday Valley Skiers! The quaint Ski Town EVL: Village of Ellicottville and Holiday Valley never disappoint! Everyone that gathers there, are friendly on the slopes & in the Village!! I respect Dennis, his wife Jane, and the Founders/Board of DirectorsHoliday/Winsum Skicorp! Their purposeful ANNUAL reinvestments, to the their infastructure, keeps Holiday Valley TOP NOTCH in the Skiing industry!! I have skied out West many times over 30 years, but always remained grateful that Holiday Valley is so close to home! It will always be my HAPPY PLACE!
Great interview Dennis!! ⛷️❄️
I love this! I feel very fortunate for my grandparents and parents who had that adventurous spirit to try out the ski thing in the 1960s which took us to Holiday Valley and Ellicottville and I am now forever a skier. Thank you Dennis and the WinSum Ski Corp for your leadership! You have cultivated a true partnership with the community which is so very important!
I began working at The Valley in the 80’s and now have the privilege to be back 40 years later. More exciting plans in the works. Thanks, NYSkiBlog for covering Western New York.
Phil, thanks for your help in putting this together.
It has long been a goal to up our coverage of Western NY, and in the last few years we have taken steps to do it. Our CNY reporter does get to WNY and in the last few years we’ve added two reporters based near Rochester.
In addition, I’ve relocated to the Adk (and retired) and hope to spend more time in both CNY and WNY.
Hope to see you soon!